The document outlines key strategies for future-proofing legal technology projects, emphasizing the importance of maintenance, succession planning, and effective communication during staffing transitions. It features insights from various presenters on lessons learned and best practices for managing project transitions, highlighting the need for documentation and knowledge sharing. Resources and tools for facilitating successful transitions and ensuring project continuity are also shared.

1. Future-Proofing Your Projects: Maintenance,
Continuity and Succession Planning
September 14, 2016

2. Presenters
Christopher Alfano
Automated Document Producer, Illinois Legal Aid Online
Jack Haycock
Client Focused Technology Innovator, Pine Tree Legal
Assistance
Kathleen Caldwell
Website Coordinator (Retired), Pine Tree Legal Assistance
Sheila Fisher
North Penn Legal Services
Xander Karsten – Project Manager, LegalServer
Mirenda Meghelli
LHI Program Coordinator, Pro Bono Net

3. Roadmap
● Mirenda will introduce the presenters and themes of the webinar
● Kathleen and Jack will cover successful legal technology projects
developed in the past and how to transition them when staffing
changes
● Chris will cover present strategies used at Illinois Legal Aid Online
to maintain and support their forms project
● Sheila will cover considerations for planning a future legal
technology project
● Xander will wrap up the presentation with transition planning
considerations that can be used at the beginning, middle or end
of a project

4. Lessons Learned from Family Leave
- Utilize existing resources; don’t re-invent the
wheel: I borrowed Xander’s transition memo as a
template for my coverage memo
- Set aside time to document and review: allow your
colleagues an opportunity to ask questions while you
are still around; what is clear to you may not be clear
to everyone
- Notify who you work with well before you leave:
inside and outside the office
- Be flexible and prepare for different scenarios: the
baby comes when they are ready
- Make like a tree...: prepare for the leave, then leave
and trust everything will be okay

5. Statewide Website Project Staff
Transition Checklist
Before website coordinator / admin leaves:
● Get stakeholder committee list
● Find out date and agenda items for next stakeholder meeting
● Advocate site membership policy -- is there one? Get a copy.
● Discuss and document transitional project priorities, for example:
● Content review
● Milestone reporting activities and documentation
● Outstanding marketing activities
● Get usernames and passwords for websites or other tools (e.g. social media),
as needed

6. Statewide Website Project Staff
Transition Checklist (cont’d)
After coordinator / admin leaves:
● Deactivate former admin’s user account on LawHelp and probono.net sites
● Replace LawHelp feedback email under Site Set Up –> My State
● Change advocate site join and welcome email sender and signature to new admin
● Add new admin as moderator of listservs as needed; remove old admin
● Contact PBN about trainings and welcome packet for new admin
● Arrange for another project staff person to review and approve members and site
content if admin / coordinator is not replaced immediately

7. Selected Resources
● Executive Director Julia Wilson’s blog post about how OneJustice planned for the 3-
month sabbatical she look last year and dealt with knowledge transfer and
continuity: https://onejusticeblog.wordpress.com/2015/12/18/leadership-is-like-a-
box-of-chocolates/
● Sucession Planning for Nonprofits: https://www.councilofnonprofits.org/tools-
resources/succession-planning-nonprofits
● Strategies for Future-Proofing your Technology:
http://www.forbes.com/sites/forbestechcouncil/2016/02/18/eight-strategies-to-
future-proof-your-technology/#266e7d1f2560
● Managing Document Automation Projects LHI Webinar:
https://www.probono.net/link.cfm?25997

8. Staffing Transitions
A Holistic Approach (and a few other suggestions)
Kathleen Caldwell & Jack Haycock - Pine Tree Legal Assistance

9. The Background
Kathleen has (had?!) been with Pine
Tree Legal Assistance for 35 years
- 20 of those years as the website
coordinator.
Jack started as Kathleen’s intern in the
Fall of 2015 - and kept working on
projects in various capacities until
starting full-time as the website
coordinator in August, 2016.
There is a TON of information to pass
on when you have been doing a job
for 20 years - and we did our best.

10. A “Holistic”
Approach to this
Staffing Transition
For better or worse, there was
no institutional system or
protocol for this kind of
staffing transition.
Most of the time we were
working in different offices.
We don’t have a formal
system, but we do have
some best practices to
share - things we each did
that made this process
much easier.

11. Staffing Transition Best Practices
Communicate
Early
Often
Openly

12. Staffing Transition Best Practices
Transfer Institutional Knowledge
Not just what we do - why we do it
Which partnerships need to be
maintained
Past mistakes and successes
The power of 20 years of hindsight
Limitations on what you can capture

13. Staffing Transition Best Practices
Overlapping Time is Key
A good chance to address the minutia - and
the big picture
In person is the best option - but it’s possible
remotely
Use any overlapping time you have
If you don’t have any, try to advocate for
getting some - even a little bit will help

14. From the mentor’s perspective
1. It helps to love your work. If you do,
convey that.
2. Documentation - as you go. (If you
didn’t, it’s too late.)
3. A good mentee is curious, asks lots
of questions, insightful question,
dumb questions - matters not, as
long as they’re totally engaged.
4. Make mistakes.
5. Good systems help, but they don’t

15. If we had to do it
all over again...
Some project management
tools that might have made
this transition easier

16. Asana
Free for up to 15 users!
Intuitive and easy to
organize
Neat visual tools for
tracking project status
and progress
Easy to see the
development of a
project over time -
could be used in
transitions to get new
people up to speed
quickly.

17. More free, inexpensive, or worth-the-price software?
1. Google drive
2. Basecamp
3. Jira
4. Trello
5. Slack
6. Confluence

18. Tips from other programs
1. Illinois Legal Aid Online (Gwen Daniels) - “We have
weekly meetings so that everyone on the team has a
good idea of the overall enterprise. Then, when someone
leaves, we already have a lot of institutional wisdom built
in among remaining staff.”
2. For website administrators, Drupal has a documentation
module (“Revisions”). Most other systems have
something similar. Use it!
3. Who else has tips?
4. Use tools like Google Sheets to help coordinate and get

19. Staffing Transitions
can be difficult - but
they don’t have to be
miserable.

20. Future-Proofing your Future
Projects:
That’s not redundant!
By Sheila Fisher, Attorney/Template Developer,
North Penn Legal Services
sfisher@northpennlegal.org

21. Motivations for new projects?
➢ New, hot projects touted at TIG conferences and webinars
➢ Priority categories in each year’s TIG application process
➢ Desire to be leader or early adopter
➢ Outdated system which is under-performing
➢ LSC baseline technology guidelines and tech plans
➢ Grant money $$$$$ !
➢ Increasing efficiencies and cost-savings

22. So now you’re
motivated ,
but . . .
Don’t bite off more
than you can chew!

23. Considerations
(besides the glitz and glam!)
How does the new project or technology:
o Fit in with other technologies already in use?
o How much training/new skill development will be required?
o Can needs be met with existing technology?
o How will new technology advance service goals?

24. How to avoid project pitfalls
• Ask experts / get second opinions
• Ask to see demos / be demanding for specifics
• Get commitment from management for funding beyond
project term
• Get commitment from management to incorporate “project”
into program culture or service goals
• Remember tech projects aren’t money makers!

25. So when you’re
applying for a
tech grant,
be sure to . . .
Look that gift horse
in the mouth!

26. More info
The Nine Steps of Planning
a Successful Technology Project
By Kyle Andrei, Tech Soup, 2014
http://forums.techsoup.org/cs/community/b/tsblog/
archive/2014/04/22/the-nine-steps-of-planning-a-
successful-technology-project.aspx

27. Stepping Up
Stepping Back
Agnostic Transition Planning
Xander Karsten, Project Manager at LegalServer

28. ● Plan Early, Plan Often
● Know your partners
● Know your deliverables
● Know your tools
Keys to Transition Planning

29. Plan Early, Plan Often
It’s never too late-
And it’s never too early!
Plan Early, Plan Often

30. Looking at the whole of the
project-
Who understands where piece of the
project is?
Who could absorb some or all of the
project?
What documentation would they
need?
Who can help make sure they are
successful?
Succession Planning

31. For each person/partner
Share email address and phone
numbers
What is their role, AND who will
step in or play backup?
Who to contact if I REALLY need
someone?
Know your Partners

32. Lay out in a public document who on the team is
responsible for what part of the project
Identify who will be their backup (either internally or
externally)
Analyze if one person or group is responsible for too
much
Accountability Matrix/Responsibility Charting

33. Know your deliverables
Make goals or deliverables
transparent & accessible
Review, revisit and rework
often and with the group.
Start with where you want to
be, and plan from there!

34. ● Does it meet your needs?
● Is it easy to maintain?
● Do your partners know and understand it?
What is your the best tool?
Know your tools

35. Short
Clear
Concise
Often
Communication

36. Meetings are only as powerful as follow up- If there isn’t
follow up, it didn’t happen.
What about meetings?

37. Final Thought...

38. Take Aways
The time to plan is now
Know your partners, deliverables and tools
Be kind
XKarsten@LegalServer.org

39. THANK YOU FOR ATTENDING
TODAY!
Next up by PBN:
Let the User be Your Guide
October 19 @10am PT/1pm ET
More information at www.lsntap.org

40. Contact Information
Brian Rowe (brianr@nwjustice.org) or via chat on www.lsntap.org
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